Hydrochloric Acid → 5-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1H-pyridin-2-one

HRID 333854Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:25])[C:11]([C:17]1[CH:18]=[N:19][C:20]([O:23]C)=[CH:21][CH:22]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].Cl.CCOC(C)=O.O>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:25])[C:11]([C:17]1[CH:22]=[CH:21][C:20](=[O:23])[NH:19][CH:18]=1)([OH:16])[C:12]([F:14])([F:15])[F:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-(2-chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(6-methoxy-pyridin-3-yl)-butan-2-ol (Example 193, 212 mg) in dioxane (8.5 ml) was added concentrated aqueous HCl (0.934 ml). The mixture was stirred at 100° C. for 1 h. After cooling to room temperature, EtOAc and water were added and the mixture was extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated to dryness to give the title compound (207 mg) as a colorless solid. MS (m/e, ISP neg. ion)=360.0 [M−H+].

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted with EtOAc
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-d0efef3ab18842f98c53c8d49e95c57f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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